Photo by Cameron Abbott

Search Cabin Rentals in Upper Matecumbe Key

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11
In one month
Jan 23 - Jan 25
In two months
Feb 20 - Feb 22
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

Water view
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1602)
"The entire resort was wonderful."
Canada
Mat
The price is ₩279,807
₩398,035 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Chesapeake Beach Resort
Exterior
La Jolla Resort

La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (1000)
"Great stay. Friendly staff, great accommodations, very nice complex. "
United States
Shela
La Jolla Resort
Property grounds
Sunset Inn

Sunset Inn

Sunset Inn
3.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1000)
"Room was clean and staff was helpful"
United States
Robert
The price is ₩230,491
₩275,959 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Sunset Inn
Exterior
Islander Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1002)
"The resort was perfect Everyone from checking in and during our stay could not have been nicer and helpful"
United States
Theresa
The price is ₩652,415
₩833,872 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Islander Resort
Aerial view
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1267)
"Friendly staff and beautiful property !"
United States
ron
The price is ₩348,060
₩489,643 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Amara Cay Resort
Exterior
Breezy Palms Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (590)
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "
United States
Terry
The price is ₩218,325
₩322,329 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Breezy Palms Resort
Exterior detail
Hadley Resort and Marina

Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1000)
"Comfortable stay. Great location. "
United States
Anand
The price is ₩220,116
₩295,926 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hadley Resort and Marina
Reception
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1278)
"Fabulous waterfront, activities, and dining as well as the staff. "
Canada
David
The price is ₩590,548
₩772,612 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cheeca Lodge & Spa
Exterior
Pines & Palms Resort

Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1001)
"Staff are excellent, resort has been recently upgraded. Best describe his quaint, comfortable and cozy."
Canada
scott
Pines & Palms Resort
Exterior
La Siesta Resort & Villas

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1001)
"Great stay and beautiful space"
United States
Amir
The price is ₩308,705
₩445,540 total
includes taxes & fees
Jan 6 - Jan 7, 2026
La Siesta Resort & Villas
Front of property
Sands of Islamorada

Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (392)
"The rooms were recently remodeled and very nice. People are really nice."
United States
Tammie
The price is ₩267,426
₩320,808 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Sands of Islamorada
Aerial view
The Islands of Islamorada

The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.8 out of 10, Exceptional, (70)
"Great for family vacation with kids. love it"
United States
Dixania
The price is ₩899,791
₩1,093,712 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Islands of Islamorada
Exterior
Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
8.8 out of 10, Excellent, (401)
"Beautiful stay!!!"
United States
Lakyne
The price is ₩426,260
₩579,447 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Bayside Villas by Islander Resort
Exterior
Casa Morada

Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (415)
"always a pleasant stay."
United States
robert
The price is ₩536,155
₩693,651 total
includes taxes & fees
Dec 24 - Dec 25
Casa Morada
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Matecumbe Key Hotel Reviews

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"Beautiful chilled out hotel"
Jacqueline 2-night trip
Posted 6 hours ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
12,001
Accommodation
0 Cabin Rentals
Lowest Price
₩275,959
Highest Price
₩1,093,712

Frequently asked questions

Are there cheap cabins in Upper Matecumbe Key?
Whether you want to stay steps from the water or on the top of a mountain, we have an awesome variety of cheap cabins in Upper Matecumbe Key to suit your budget and taste. Priced from ₩275,959 to ₩1,093,712 per night, your ideal cabin is waiting right here. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the highest-rated cabins in Upper Matecumbe Key?
Expedia cabin travelers just keep coming back to Cabin - Sand Is The New Snow - New 4bedroom W. This top pick features a host of handy amenities including a private pool and a deck. It won't take you very long to see why Historic, Dog - Friendly Cottage In The Heart Of Key West W is also popular with vacationers. Conveniences such as a patio and a deck will help make your stay nice and comfortable.
Why should I book a cabin in Upper Matecumbe Key?
Affordability, outdoor attractions, rustic charm — there are countless great reasons to book an Upper Matecumbe Key cabin. Escape the noisy concrete jungle and wake up to the beautiful sounds of Mother Nature. There's so much adventure just around the corner too. Whether you're taking a break with friends, family or your partner, you'll find the perfect rental cabin on Expedia.
What are the top nature cabins in Upper Matecumbe Key?
Spend a few nights at Cabin - Sand Is The New Snow - New 4bedroom W and you'll be surrounded by nature. Amenities like a private pool and a deck help make this river cabin in Upper Matecumbe Key a top option. Historic, Dog - Friendly Cottage In The Heart Of Key West W is another place where you can escape the hustle and bustle and catch a few mindful moments by the water. Some of the conveniences here include a patio and a deck.